Pyridine → HCID 22291039, compound

HRID 967874Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[NH2:6][C:7]1[CH:8]=[C:9]([NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=2)[CH:10]=[CH:11][C:12]=1Cl.[CH2:25]([O:27][CH2:28][CH2:29][O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)[CH3:26].N1C=CC=C[CH:41]=1>O>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:9]2[CH:10]=[CH:11][C:12]([CH3:41])=[C:7]([NH:6][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][C:31]([O:30][CH2:29][CH2:28][O:27][CH2:25][CH3:26])=[CH:32][CH:33]=3)[CH:8]=2)=[O:24])=[CH:17][CH:18]=1)#[N:23]

Participants

Conditions

Temperature: -15 °C

Procedure

Phosphoryl chloride (0.03 ml) was added dropwise to a stirred mixture of N-(3-amino-4-chlorophenyl)-4-cyanobenzamide (0.08 g), 4-(2-ethoxyethoxy)benzoic acid (J. Org. Chem., 1973, 38, 3160; 0.062 g) and pyridine (4 ml) which had been cooled to −15° C. The reaction mixture was stirred at −15° C. for 3 hours and then allowed to warm to ambient temperature. The mixture was stirred for 48 hours. The reaction mixture was diluted with water and stirred overnight. The precipitate was isolated, washed with diethyl ether and dried under vacuum at 55° C. to give the title compound (0.024 g); NMR Spectrum: (DMSOd6) 1.15 (t, 3H), 3.49 (m, 2H), 3.73 (m, 2H), 4.19 (m, 2H), 9.86 (s, 1H), 10.62 (s, 1H); Mass Spectrum: M−H− 462.

Workup

temperatureto warm to ambient temperature
stirringThe mixture was stirred for 48 hours
stirringstirred overnight
customThe precipitate was isolated
washwashed with diethyl ether
customdried under vacuum at 55° C.

Sources & evidence

ORD record: ord-901e6a11c8a140dca6dfea0955aa69e9
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956037B2

Reaction notes

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